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I've had it with the tendentious editing from IP addresses. I've requested semiprotection. Jytdog (talk) 07:13, 8 December 2014 (UTC)[reply]

 Done. I made it indef not because I think it should be infinite, but because it's a long-term problem and the good-faith editors need an uncertain amount of breathing room to see if there are any improvements at hand. No objection (== "need not consult with me first") to other admins converting to indef/long-term pending-changes or setting an endpoint to the semi. DMacks (talk) 07:24, 8 December 2014 (UTC)[reply]

thank you! Jytdog (talk) 08:59, 8 December 2014 (UTC)[reply]

Thanks DMacks. I was about to request this myself - both methamphetamine and amphetamine are permanently semi-protected anyway, so there is a precedent for an indefinite lock here. Seppi333 (Insert 2¢ | Maintained) 09:36, 8 December 2014 (UTC)[reply]

Its fine to have a sentence or two about how organic compounds are synthesized, but we generally do not provide the level of detail that was added here per WP:NOTAGUIDE. In the case of referring to specific named organic reactions and reagents, this sort of thing goes way over the head of 99% of our readers in any case. And as one of the 1% who does understand this material, I'd generally go to other sources and not Wikipedia when looking for synthetic information.

Yes, you can find examples of fairly detailed synthesis descriptions in some articles, but these are generally removed within a day or so of being added as I have here, for the above reasons. See for example the diffs below.

https://en.wikipedia.org/w/index.php?title=Tetracycline&diff=639920650&oldid=639815940 https://en.wikipedia.org/w/index.php?title=Benzoctamine&diff=prev&oldid=640281520 https://en.wikipedia.org/w/index.php?title=Lometraline&curid=35642404&diff=640281098&oldid=640264636 Formerly 98 (talk) 08:42, 1 January 2015 (UTC)[reply]

I don't personally care as long as we are consistent with similar articles. Methamphetamine also has a pretty substantial synthesis section which should be pared down under this reasoning.Sizeofint (talk) 09:45, 1 January 2015 (UTC)[reply]

Well, I tried to trim that out and got slapped down, as it has been designated a "Good Article". So I am going to back off a little bit here and just ask that you try to keep a cap on the technical details and name reactions. Thanks for the discussion. Formerly 98 (talk) 13:53, 1 January 2015 (UTC)[reply]

Alright, I will add it back in and see if I can simplify the section. Sizeofint (talk) 23:56, 1 January 2015 (UTC)[reply]

I added my thoughts on synthesis sections in articles like MDMA here: Special:Permalink/640752702#Synthesis section. I personally don't really care if such a section is included in a few articles like this, but it may be worth starting the dialogue I mentioned to establish a concrete policy on the coverage of synthesis routes in articles on US/UN schedule 1 controlled substances (globally banned chemicals). Seppi333 (Insert 2¢ | Maintained) 04:05, 3 January 2015 (UTC)[reply]

There seems to be an edit war over which image this article should use. The top one shows the double bonds but the bottom one shows some hidden atoms. Anyone have comments regarding this.

Sizeofint (talk) 19:45, 8 January 2015 (UTC)[reply]

I don't want to say a lot to sway public opinion on this. I appreciate the call to discuss. If you look at the top picture, the hidden atoms are not entirely hidden. You have to view the larger resolutions to see them clearly but they are at least partially visible, it's because of the angle of the image that they're not as obvious in the thumbnail. Lazord00d (talk) 16:58, 9 January 2015 (UTC)[reply]

The top image does not accurately depict the bonding in a benzene ring, showing alternating single and double bonds. The bottom image, which I made some years ago, shows the the C-C bonds in the ring are more or less equivalent in length and strength. I would strongly encourage those without a strong chemistry background not to get involved in making molecular models, as it leads to inaccuracies like this. --Ben (talk) 18:32, 10 January 2015 (UTC)[reply]

I agree with Ben. I have no objection to using normal single/double-bond styling for regular skeletal diagrams (the top), even though the bonds are not truly like that. But if one were to use them in any sort of more sophisticated style that includes geometry, every bond-length in that ring must be equal and the presence of the "second" bond of a double bond should not displace the position of the "first" bond (note that these detail is true even in the single/double diagram). It's okay not to know that this ring is not actually single and double bonds, and it's okay in some contexts to illustrate it that way, but anything built on top of that factually flawed detail becomes increasingly incorrect--and visibly so--in many ways. See benzene and aromaticity to learn more. The double-bonds really approximately do circulate around the ring, as the lower diagram illustrates, and the perspective is better in that the back atoms are more readily visible even at thumbsize. DMacks (talk) 20:12, 10 January 2015 (UTC)[reply]

Okay, if there aren't any objections in the next day or so I'll switch the image to the bottom one. Sizeofint (talk) 00:19, 11 January 2015 (UTC)[reply]

The bond lengths in the images I've submitted are determined by the software's built-in algorithm and the size settings for the atom diameter.. as I didn't write it I can't speak for it's accuracy, however jmol is well known and I trust its programmers much more than any reference in this thread I can say that for sure. Also, even though the points about aromaticity are factual, my position is that the fact that the stick and ball models I've submitted are closer to the 2d model makes them more easily understood. I can't support reverting based on that criteria but this is a public forum so it's not up to me what happens ultimately and honestly constantly defending edits gets old and boring when there is no real challenge and life is passing by. I'd rather enjoy it than argue back and forth about stuff that essentially boils down to opinion of people who have zero credibility that I have seen in real life. Have any of you posted your diplomas anywhere lol? Really I would expect much more substance in your rebuttals (which would of course take optical phenomena caused by different shaped structures on each side of connected spheres into account now wouldn't they? ;-) the concept is as old as the circle & square illusion) but hey it's whatever.. Y'all have fun now! I mean that too. Enjoy life! :-)

Lazord00d (talk) 05:02, 11 January 2015 (UTC)[reply]

To be blunt, that you have only been able (thus far) to find settings that make chemically incorrect results or only fed it chemically incorrect input is not our problem. Every molecular modelling package (even the heavy-weight quantum computing ones) and every attempt to do something blindly/automatically from a skeletal structure (such as PubMed or related indexing) can and often does give wrong (sometimes wildly wrong) structural results if the initial parameters are not correct--we've seen examples on wikipedia of tangled rings, atomic collisions, and bonds intersecting each other. I would tolerate a single/double 3D diagram and certainly value making something clearer, but not at the expense of amplifying other incorrect aspects. Readers have a funny habit of putting trust in what they read; I think it's a horrible choice to make something more incorrect (with no other aspect being made more correct to compensate) just to be more understandable (especially when what's being made "more understandable" is not correct in the first place). What matters on wiki is what's on-wiki and what's citeable (WP:V policy)--we can all read literature and you can choose to avoid continuing to be a victim of GIGO. DMacks (talk) 10:53, 11 January 2015 (UTC)[reply]

Note that Jmol has a feature for measuring atomic distances, so you can measure for yourself whether the C–C and C=C are actually equal lengths (and just displayed with optical illusions). There's some science: I made an observation about your results, you proposed an alternate hypothesis to explain it; but you have the actual underlying data, so go prove it one way or another. Though why one would think that an image subject to optical illusions that suggest there are factual mistakes is better than one that doesn't is beyond me (especially if your claim is that this all is to better-illustrate it!). DMacks (talk) 10:59, 11 January 2015 (UTC)[reply]

Ahh there you go! Substance. Congratulations you're the first. Yay for you! But I'm still not waving my white flag :-)...

My interest in uploading images in the first place was to try to standardize some of the hodgepodge that's out there in terms of molecular visualization, so I thought about what variation would be the most beneficial to the most users and this is what I ended up with.. pretty much zero% of users will have thought about this as much as you or I have which is the reason I ended up with that result not to muddy the waters. If anything they're muddied by the randomness of the models that currently exist IMO. I have a feeling that a lot of them are inaccurate in far worse ways than mine with their double-bonds showing (oh myyyy).. this isn't a Chemistry textbook, it's an Encyclopedia. There is a difference in scope..

Lazord00d (talk) 11:31, 11 January 2015 (UTC)[reply]

At Wikipedia:Articles for deletion/Sasha Rodriguez, about an article which reports several cases of death from water intoxication after consuming MDMA, I have proposed that information about that subject be merged to this article under "Adverse effects". The sourcing at that article is not satisfactory, but a scan of Google Scholar suggests that adequate sourcing can be found. Any input to that AfD is welcome, as is any comment here about whether such a merge would be appropriate. --MelanieN (talk) 23:03, 18 January 2015 (UTC)[reply]

Hyponatremia is discussed under Adverse effects. I don't think we'd need any sources from that article, particularly since they would need to comply with MEDRS for inclusion here. I would say just delete it; a merge is probably not necessary. Sizeofint (talk) 20:00, 19 January 2015 (UTC)[reply]

It's true that "life threatening hyponatremia" is mentioned in the article. That doesn't convey much to the casual reader. I was thinking it might be important to add that death can occur and has occurred under these circumstances. I don't see any mention of death, in plain English, in the article; people reading this article might need it stated a little more clearly that you can die from this course of action. Of course the references would have to meet MEDRS (which the ones in the AfD article don't, so you're right, merge is not an appropriate suggestion), but there are articles about this in the literature. Naturally I would propose any such addition and references here before adding anything to the article. --MelanieN (talk) 21:08, 19 January 2015 (UTC)[reply]

I don't think anyone would be opposed if you want to clarify or expand on water intoxication here. Sizeofint (talk) 01:24, 20 January 2015 (UTC)[reply]

@Sizeofint: I've not reverted you because I don't want to get into that mode, but I don't think we really have a reliable source yet for the idea that the DEA investigated MDMA use and never caught wind of its therapeutic use, which I think is a pretty extraordinary claim. The first reference is at least partly self-published, which flushes it immediately per WP:RS. The second is a legitimate publication, but what is says is "some guy in the DEA said they didn't know" which really does not support anything, as one can always find "some guy" willing to attest to just about anything. I don't mind the "DEA was surprised by the level of opposition", but the "DEA had no clue" part really just seems weak to me and in need of a stronger source if we are going to include it here. thanks Formerly 98 (talk) 00:24, 1 February 2015 (UTC)[reply]

@Formerly 98: I understand your concerns. I've reviewed the sources that claim the DEA was unaware of the therapeutic use of MDMA in 1984. All eventually link back to a Newsweek article published in April 1985 in which the DEA pharmacologist makes his statement. I have changed the text so it indicates the information originates from this single pharmacologist. Thanks for taking time to discuss. Sizeofint (talk) 03:08, 1 February 2015 (UTC)[reply]

The paragraph I added the primary source to already has two primary sources citing neurotoxic effects; I do not understand why a primary source citing the cause of neurotoxicity would not be relevant. If secondary sources must be used, then the whole section should be deleted. This rule should either apply across the board or not. Please review WP:MEDRS; secondary sources are not a requirement. — Preceding unsigned comment added by Morrowfolk (talk • contribs) 00:47, 13 February 2015 (UTC)[reply]

@Morrowfolk: The second paragraph of WP:MEDRS states: " Primary sources should generally not be used for medical content. [Bolding in original]. Many such sources represent unreliable information that has not been vetted in review articles, or present preliminary information that may not bear out when tested in clinical trials."

Further down this message is repeated. "Primary sources should generally not be used for health related content, because the primary biomedical literature is exploratory and not reliable - any given primary source may be contradicted by another, and the Wikipedia community relies on the guidance of expert reviews, and statements of major medical and scientific bodies, to provide guidance on any given issue."

If there are other statements in the paragraph that are supported solely by primary sources, I will fully support their removal. Formerly 98 (talk) 01:34, 13 February 2015 (UTC)[reply]

Formerly 98 (talk) 01:34, 13 February 2015 (UTC)[reply]

I forgot to sign my last post, my apologies. Anyway, I am referring to this quote:

"If the conclusions of the research are worth mentioning (for instance, publication of a large, randomized clinical trial with surprising results), they should be described as being from a single study, for example:

"A large, NIH-funded study published in 2010 found that selenium and Vitamin E supplements increased the risk of prostate cancer; it was thought they would prevent prostate cancer." (citing PMID 20924966)

After enough time has passed for a review in the area to be published, the review should be cited in preference to the primary study. Using a secondary source often allows the fact to be stated with greater reliability:

"Supplemental Vitamin E and selenium increase the risk of prostate cancer." (citing PMID 23552052)

If no review on the subject is published in a reasonable amount of time, then the content and primary source should be removed."

The citation in question was published in a journal that does not promote an agenda, and certainly had surprising results. However, it is from 2011 and does not have a review that I can find. There are a few comments, but that is essentially it. I do not see refutation of the data... Is three years too long? "Reasonable amount of time" is vague.

Thank you for the clarification of your views; I was initially very annoyed because many users post rules as a means of maintaing a certain view in an article, but you make it clear that you are simply attempting to improve the quality of medical articles. Morrowfolk (talk) 18:33, 13 February 2015 (UTC)[reply]

The main reason we're not going to include that is because it refutes what the reviews conclude, where most of those neurotoxicity reviews are 2-3 years more current than that primary source. Seppi333 (Insert 2¢ | Maintained) 21:06, 13 February 2015 (UTC)[reply]

Edit: btw, there are a couple newer primary sources like PMID 23194825, PMID 24101030, and PMID 24177245 which suggest MDMA also produces dopamine neurotoxicity through its metabolites. We don't include these either simply because they're primary sources. Seppi333 (Insert 2¢ | Maintained) 21:10, 13 February 2015 (UTC)[reply]

In the text it both says molly means the pure form and other things - this is directly in contradiction with each other. It can't mean the unadulterated form if it also means other drugs! "The UK term "Mandy" and the US term "Molly" colloquially refer to MDMA in a crystalline powder form that is relatively free of adulterants.[5][6] "Molly" can sometimes also refer to the related drugs methylone, MDPV, mephedrone or any other of the pharmacological group of compounds commonly known as bath salts.[12]" This pair of sentences would probably be better to say that the name was given to one but has expanded on the street to mean any of these such as:"The UK term "Mandy" and the US term "Molly" colloquially refer to MDMA[5][6], however "Molly" can sometimes also refer to the related drugs methylone, MDPV, mephedrone or even any other of the pharmacological group of compounds commonly known as bath salts.[12]" ...which then wouldn't contradict itself by saying it was the colloquially pure when it can mean all the others which are colloquially not pure. A statement that the street form is usually a tablet or encapsulated powder probably should be in a different sentence not contradicting itself. 76.21.107.77 (talk) 19:55, 23 February 2015 (UTC)[reply]

A couple of points here:

• The first statement says "colloquially", which implies that it is vernacular and/or slang, and therefore not always or even generally accepted;
• The second statement says "'Molly' can sometimes refer to (object)"; the word "can" is not the same as the word "must", which implies that it doesn't always refer to (object).
• (edit) What, pray tell, does "colloquially pure" mean?

This is basic English grammar, and I'm tired of this silly argument over "MDMA" vs "Molly". "MDMA" clearly and unambiguously describes the chemical which is the subject of this article. Street names are relevant to the discussion but ultimately a distraction. If you don't like it, you're free to change it, but please don't do it from an anonymous IP. Simishag (talk) 22:42, 23 February 2015 (UTC)[reply]

MANDY was ENGLISH name for a prescribed drug with the TRADE NAME MANDRAX ( a sedative containing METHAQUALONE & DIPHENHYDRAMINE HYDROCHLORIDE ). The GERMAN ARMY was EXPERIMENTING with MDMA in 1934 . — Preceding unsigned comment added by 134.2.64.114 (talk) 18:46, 2 March 2015 (UTC)[reply]

I can tell you that the sources I have read do not mention experimentations with MDMA in 1934. It is possible they were experimenting with MDA however. Sizeofint (talk) 18:51, 2 March 2015 (UTC)[reply]

I am not sure about Mandy as a slang term, however Urban Dictionary lists powdered MDMA as the most popular definition of Mandy. Granted, UD is not a reliable source but it indicates the term is plausible. Sizeofint (talk) 18:57, 2 March 2015 (UTC)[reply]

A quick Google News search turns up numerous references that indicate "Mandy" is indeed a slang term for MDMA, particularly in the UK. -- Ed (Edgar181) 19:05, 2 March 2015 (UTC)[reply]

Please change "has potential adverse effects, such as neurotoxicity and addiction" to "has potential adverse effects, such as neurotoxicity and transient addiction" as that is what the source claims.

Although these findings may not apply to all groups of ecstasy users, they suggest that ecstasy abuse and dependence may be transient phenomena in many, if not most, instances. - Meyer, J. in 3,4-methylenedioxymethamphetamine (MDMA): current perspectives

Boddika (talk) 15:28, 8 March 2015 (UTC)[reply]

Dependence is not addiction. Seppi333 (Insert 2¢ | Maintained) 22:43, 8 March 2015 (UTC)[reply]

But isn't dependence required for addiction? Either way, seems like the main issue is the lack of the word "transient", which was not addressed. SaltyRide (talk) 16:24, 15 March 2015 (UTC)[reply]

Not done: please establish a consensus for this alteration before using the {{edit semi-protected}} template. — {{U|Technical 13}} (e • t • c) 22:06, 15 March 2015 (UTC)[reply]

Dependence and addiction are 2 entirely different concepts. The ref makes no statement at all about addiction. Seppi333 (Insert 2¢ | Maintained) 23:26, 15 March 2015 (UTC)[reply]

I noted a citation was needed for the claim that MDA is a "direct neurotoxin". The reference added by Seppi333, actually a compendium of abstract-style summaries of primary literature, does not seem to support the claim. The first appearance of the word MDA claims to be a peer reviewed citation, but it's actually an unreviewed government website and the word "MDA" appears to be a typo:

"Research shows that MDA destroys serotonin-producing neurons in the brain, which play a direct role in regulating aggression, mood, sexual activity, sleep, and sensitivity to pain. It is probably this action on the serotonin system that gives MDMA its purported properties of heightened sexual experience, tranquility, and convivality. [National Institute on Drug Abuse (NIDA) Infofax on ECSTASY. Available from http://www.nida.nih.gov/Infofax/ecstasy.html on Wednesday, May 17,2000] **PEER REVIEWED* "

This is obviously not peer reviewed. The linking of MDA in the first sentence with "this action" in the second makes it clear that MDA is a typo and that they meant to write MDMA. Moreover, the sentence about MDA does not appear on the website, as far as I can tell. I suggest that Toxnet be deprecated in favor of more reliable refernces. The vast majority of the papers it mentions seem to be about MDMA and many describe NIH-funded studies where volunteers were given MDMA. The only other mention relevant to MDA toxicity I see seems to state the opposite of the original claim:

"Direct injection of either 3,4-(+/-)-methylenedioxymethamphetamine (MDMA) or 3,4-(+/-)-methylenedioxyamphetamine (MDA) into the brain fails to reproduce the serotonergic neurotoxicity seen following peripheral administration."

I propose adding in the citation needed tag or removing the sentence, which has only peripheral relevance since it isn't about MDMA. 173.228.54.200 (talk) 04:56, 26 November 2014 (UTC)[reply]

I corrected the issue with species earlier which had been incorrectly stated. The current version is in accordance with the source, so I'm not going to revise this further. Seppi333 (Insert 2¢ | Maintained) 05:10, 26 November 2014 (UTC)[reply]

I'm sorry, can you clairify what you mean by "the issue with species"? I have pointed out that the references you gave do not support the claim the MDA is a neurotoxin. Do you believe they do? 173.228.54.200 (talk) 05:16, 26 November 2014 (UTC)[reply]

https://en.wikipedia.org/w/index.php?title=MDMA&diff=635435983&oldid=635414760 - notice the timestamp relative to your post. I'm not sure what the issue with the current revision is. Seppi333 (Insert 2¢ | Maintained) 05:22, 26 November 2014 (UTC)[reply]

Actually, given that this is nonhuman animals, I'm just going to delete the clause. Neurotoxicity in animals doesn't necessarily reflect upon humans by any means. Seppi333 (Insert 2¢ | Maintained) 05:37, 26 November 2014 (UTC)[reply]

The issue was that the reference does not support any neurotoxicity from MDA, only MDMA. And I have a secondary concern that the reference is unreliable since it claims un-reviewed goverment websites were peer reviwed and it has important typos. I suggest Toxnet be depricated as a reference. 173.228.54.200 (talk) 05:38, 26 November 2014 (UTC)[reply]

Toxnet satisfies WP:MEDRS. Trying to argue this point is going to get you nowhere. Seppi333 (Insert 2¢ | Maintained) 05:40, 26 November 2014 (UTC)[reply]

Interesting. Can you explain how Toxnet fits that WP? It isn't clear to me that it does. And it appears to me that its value is questionable. The first thing you/they cited mentioned the wrong drug through a typo and claimed an unreviewed web article was peer-reviewed. How can this be alleged to be reliable? And there seems to be no recourse for correcting it: In the FAQ, Toxnet says that non-Pubmed parts cannot be corrected because they are not produced by the NLM. Regards, 173.228.54.200 (talk) 05:51, 26 November 2014 (UTC)[reply]

I'm not going to argue over this. Ask about the source here if you actually want to push the issue: WT:MED. Seppi333 (Insert 2¢ | Maintained) 05:56, 26 November 2014 (UTC)[reply]

Done. Thanks for the pointer. 173.228.54.200 (talk) 06:05, 26 November 2014 (UTC)[reply]

I agree that Toxnet is not a reliable source per WP. It obscures the actual sources. SaltyRide (talk) 04:54, 11 March 2015 (UTC)[reply]

The Medical section currently reads as: MDMA currently has no accepted medical uses.[13][17] which is semi-correct but very sparse and misleading!

The last paragraph of the opening section relates to medical history and in my opinion should be moved to the Medical section.

Plus the DEA have recently approved trials into MDMA for seriously ill patients, so a note that the current status is always under review and flux would be a good idea.

So my proposed changes to the section would read as thus (or very similar):

Although at the current time MDMA is scheduled as Class I in the USA and the official state is it "has no accepted medical uses"[13][17] (with general worldwide agreement, see Legal Status section) there are DEA and other approved trials into its effectiveness in PTSD and other serious illnesses,[*1] which in the past have often had positive results.[*2] MAPS (the Multidisciplinary Association for Psychedelic Studies) hopes to make MDMA a FDA approved precription medicine by 2021.[*3]

In previous trials medical reviews have noted that MDMA has some limited therapeutic benefits in certain mental health disorders, but has potential adverse effects, such as neurotoxicity and cognitive impairment, associated with its use.[15][16] Further research will help determine if its potential usefulness in posttraumatic stress disorder (PTSD) treatment outweighs the risk of persistent neuropsychological harm to a patient.[15][16]

---

[*1] http://www.huffingtonpost.com/2015/03/18/dea-mdma-study_n_6888972.html [*2] http://www.usatoday.com/story/news/nation/2014/07/11/mdma-molly-therapy-ptsd-cure/10683963/ [*3] www.maps.org/research/mdma

Please review and edit if you agree these changes would make sense. Sorry I have never signed up and only ever done a small handful of minor edits in my life, with this being a Protected article here I can't so I hope you don't mind me going via this method instead. I know it's still a but messy but as I can't post directly hopefully somebody who agrees can tidy it up that last iota... — Preceding unsigned comment added by 101.99.4.59 (talk) 08:52, 9 April 2015 (UTC)[reply]

For content to be in the medical uses the general guideline is that it have at least reached clinical trials. The ongoing pilot studies by MAPS are noted in the research section at the end of the article. Sizeofint (talk) 16:49, 9 April 2015 (UTC)[reply]

I'd like to see a better source for this than Playboy Magazine. As a chemist, I can say that its very, very tough to get a position, let alone tenure at MIT or Harvard. And the people who succeed are generally not of the type who will put their careers at risk for social missions of the sort described in the article: they are more typically single minded careerists who would never take this kind of risk. The credibility of this story is not increased by the continuation of the story in the source, which states that "they were threatened by some very dangerous people and had two days to leave the country". A mass departure of tenured faculty from the two of the top five chemistry departments in the country would have made the newspapers, let alone the industry newsletters that I followed religiously during that period. This entire section of the article seems to be based on an urban myth, not scholarly research into the history of the drug. Formerly 98 ^{talk|contribs|COI statement} 17:19, 28 April 2015 (UTC)[reply]